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Kaupulehu Vacations

Pack those stellar shades. We have Kaupulehu vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Kaupulehu – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Kaupulehu vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Kaupulehu

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Kaupulehu vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Kaupulehu well.

Top Hotel Deals

See all 1,465 Hotels in Kaupulehu
Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

72-100 Ka'upulehu Drive, Kailua-Kona
    5.0 out of 5.0
     
     

    Nestled along the Kona-Kohala Coast with a beach, the luxury resort is 7 mi (11 km) from the airport, 21 mi (34 km) from Holualoa Village, and 99 mi (159 km) ...

    Four Seasons Resort Hualalai$839

    Four Seasons Resort Hualalai$839
    129B Hualalai

    129B Hualalai

    72-129B Kaulu Street, Kailua-Kona
      4.0 out of 5.0
       
       

      Situated in Kailua-Kona, this condo building is within 6 mi (10 km) of Mahai'ula Beach, Kua Bay, and Manini'owali Beach. Kekaha Kai State Park and Makalawena ...

      104A Waiulu Street Hualalai

      104A Waiulu Street Hualalai

      104A Waiulu Street, Kailua-Kona
        4.5 out of 5.0
         
         

        Situated in Kailua-Kona, this luxury condo building is within 6 mi (10 km) of Mahai'ula Beach, Kua Bay, and Manini'owali Beach. Kekaha Kai State Park and Makalawena ...

        115D Waiulu Street Hualalai

        115D Waiulu Street Hualalai

        115D Waiulu Street, Kailua-Kona
          4.0 out of 5.0
           
           

          Situated in Kailua-Kona, this condo building is within 6 mi (10 km) of Mahai'ula Beach, Kua Bay, and Manini'owali Beach. Kekaha Kai State Park and Makalawena ...

          120A Waiulu Street Hualalai

          120A Waiulu Street Hualalai

          120A Waiulu Street, Kailua-Kona
            4.0 out of 5.0
             
             

            Situated in Kailua-Kona, this golf condo building is within 6 mi (10 km) of Mahai'ula Beach, Kua Bay, and Manini'owali Beach. Kekaha Kai State Park and Makalawena ...

            Pu'u Kole Street Home Unit 106 by RedAwning

            Pu'u Kole Street Home Unit 106 by RedAwning

            72-106 Pu'u Kole St., Kailua-Kona
              3.5 out of 5.0
               
               

              Situated in Kailua-Kona, this vacation home is close to Manini'owali Beach and Kua Bay. Area attractions also include Queen's Bath and Makalawena Beach.

              Hainoa Villa 2905D by RedAwning

              Hainoa Villa 2905D by RedAwning

              72-2905D Hainoa Street, Kailua-Kona
                4.0 out of 5.0
                 
                 

                Situated in Kailua-Kona, this villa is close to Manini'owali Beach and Kua Bay. Area attractions also include Makalawena Beach and Kekaha Kai State Park.

                Palm Villa 126B

                Palm Villa 126B

                72-126 Waiulu Street, Unit 126B, Kailua-Kona
                  3.5 out of 5.0
                   
                   

                  Situated in Kailua-Kona, this condo building is within 6 mi (10 km) of Mahai'ula Beach, Kua Bay, and Manini'owali Beach. Kekaha Kai State Park and Makalawena ...

                  Hainoa Villa 2905A by RedAwning

                  Hainoa Villa 2905A by RedAwning

                  72-2905A Hainoa Street, Kailua-Kona
                    4.0 out of 5.0
                     
                     

                    Situated in Kailua-Kona, this condo building is close to Manini'owali Beach and Kua Bay. Area attractions also include Makalawena Beach and Kekaha Kai State ...

                    Waiulu Villa 119C by RedAwning

                    Waiulu Villa 119C by RedAwning

                    72-119C Waiulu Street, Kailua-Kona
                      3.5 out of 5.0
                       
                       

                      Situated in Kailua-Kona, this villa is close to Manini'owali Beach and Kua Bay. Area attractions also include Makalawena Beach and Mahai'ula Beach.

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.